Boston Red Sox general manager Ben Cherington smiles after the Red Sox won the World Series in October. (Bob DeChiara-USA TODAY Sports)

A morning after his slice of immortality had been clinched, Ben Cherington went to work. They'd barely finished clearing the corks from the clubhouse floor, the parade was not yet planned, and the rest of Boston blearily awoke with the happiest of hangovers - but there was little time for the Red Sox general manager to bask in the bliss of a World Series championship, because baseball was on the brink of its winter.

"Free agency started the next morning," the Meriden native told the crowd during a town hall-style event at Northeastern University last Wednesday - the same night the signing of veteran outfielder Grady Sizemore offered a reminder that 12 weeks later free agency is still ongoing. And that Cherington's work still isn't done.

Now 25 days from the first full-squad workout of spring training, the Red Sox still have plenty to do and determine from a personnel perspective before they're ready to begin their title defense on the final day of March, even if Cherington is being genuine when he says he's comfortable opening the season with his roster as currently constituted. Nothing is make or break, necessarily, and certainly the club could - and should - remain competitive if the work lingers into April, but the questions touch on enough areas of the club that the sooner they're answered the better situated the Sox will be. That considered, here's one take on how the team may prioritize a lineup full of lingering personnel tasks as January nears its end:

1. Sizemore or Bradley?

With Jacoby Ellsbury having defected to the Yankees, the Sox need a center fielder - though there are significant questions about both of their current candidates. Sizemore hasn't played in the majors (or minors) since 2011, so on top of the health concerns it remains to be seen whether he can still play. Jackie Bradley, meanwhile, didn't appear especially big-league ready while hitting .189 in 37 major-league games last season. Not-yet-24, the Sox likely want Bradley to play everyday somewhere, and because both players bat left-handed, it's unlikely they'd split duties, so it'll likely be up to Sizemore to win the job by proving himself in spring training.

2. Monitor the pitching market.

The Sox still have six proven big-league starting pitchers, all of whom, honestly have tradable contracts, so Cherington should be keeping an eye on the market to see which clubs need pitching after the final free agents find homes and injuries start to arise in camp. Ryan Dempster is the most logical to be moved, though Jake Peavy and John Lackey are hardly untouchable, and Felix Doubront might fetch the most in return because of his age (26) and throwing arm (left). It's never a bad thing to have too much pitching, but given the almost-ready options in the farm system, the Sox could afford to part with a veteran.

3. Extend Jon Lester.

It's not likely to impact their win-loss record this season, but if the Red Sox have determined that they want Jon Lester to be a major part of their future - and based on last October, who could argue? - they should make an effort to reach agreement on a contract extension before the start of the season. On top of eliminating a potential distraction, another motivation could be this: If the Sox sign him before the year, they could possibly start the extension right away, and tear up this final year of the lefty's old deal. Then a, say, five-year commitment only last through Lester's age 34 season; the pitcher makes more short-term than he would have; and maybe that improves the opportunity for a both-sides-win hometown discount.

4. Deepen the left side.

At this point, the left side of the Sox infield is Xander Bogaerts at shortstop and Will Middlebrooks at third base, with Jonathan Herrera backing up both positions. The ceiling is high with that setup, but there are also likely to be some growing pains given the rawness of the two players. If the opportunity presents itself as roster cuts near elsewhere, the Sox could look to fortify those spots by adding established depth via trade.

5. Find roles for the young arms.

Brandon Workman and Drake Britton both pitched important innings out of the bullpen late last season after working almost exclusively as starters on their ascension through the minors. Cherington has said they'll report to Fort Myers as starting pitchers, but both could just as well wind up as counted-upon relievers as farm-league starters, and the sooner Sox brass can make that determination the sooner the rest of the roster will take shape.

6. Assess the bench.

Boston's bench was a strength last season, and with some combination of Daniel Nava, Mike Carp, Jonny Gomes and maybe Sizemore available on most nights, it could be again this season. However, there's a lot of redundancy in that group, so there might be more value in trading someone from that group to fill another need (such as a right-handed hitter). Carp would be the most likely to go.

7. Who leads off?

Another byproduct of Ellsbury's exit is the lack of a leadoff man. Dustin Pedroia has done it, and did it when Ellsbury was hurt last September. Sizemore, Nava and Shane Victorino have filled the role, as well, in the past. It's not a major concern, but last season the Sox seemed to benefit from stability at the top of the order - spots 1-4 all had one batter penciled in the same place for at least 107 games - so John Farrell may be inclined to identify his solution early.

8. Figure out Lavarnway.

The presence of A.J. Pierzynski and David Ross would seem to preclude Ryan Lavarnway from a role as a Red Sox catcher this season. Christian Vazquez was added to the 40-man roster after reaching Triple-A late last season and, at 23, will be there this year. If Lavarnway has any value left at age 26, the Sox may want to cash out now instead of clogging the pipeline by sending him for a fourth-year at Pawtucket.

9. Contemplate a blockbuster.

Boston has organizational depth at catcher, in the infield, and - most importantly - among starting pitchers who will soon be knocking on the big-league door. With that combination, with money, and with some holes still to fill, the ingredients are all there if the Sox want to make a blockbuster trade. So don't be surprised if, three months after the work began, Cherington's biggest move is still to come.

Dave D'Onofrio covers the Red Sox for the New Hampshire Union Leader and Sunday News. His e-mail address is ddonof13@gmail.com.